Реакция #2122468

Уравнение реакции

Calcium carbonate

Dimethylcarbamyl chloride

N-hexyl acetamide

sodium hydroxide

→

product

Выход 32.4%

N,N-Dimethyl-N′-butyl Ethanimidamide

Выход 32.4%

Растворители

toluene

water

Условия реакции

Обработка

1. 1
   ТемператураAfter being refluxed under a nitrogen atmosphere for 16 h
2. 2
   Другоеthe volatile materials were removed on a rotary evaporator
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 30 mL dichloromethane
4. 4
   ДругоеThe organic phase was separated
5. 5
   Промывкаthe aqueous phase was washed with dichloromethane (3×25 mL)
6. 6
   СушкаThe combined organic phases were dried over anhydrous calcium carbonate
7. 7
   ДругоеThe volatile materials were evaporated on a rotary evaporator
8. 8
   workup.DISTILLATIONThe residue was distilled, by 28-30° C./
9. 9
   Другое0.25 Torr (lit. bp 69-71° C./13 Torr (see Haug, E. et al. Synthesis, 1983, 35-37))

Методика

Dimethylcarbamyl chloride (9.35 g, 86.9 mmol) was slowly added to a solution of N-hexyl acetamide (10.0 g, 86.9 mmol) in 10 mL of dry toluene. After being refluxed under a nitrogen atmosphere for 16 h, the volatile materials were removed on a rotary evaporator and then in vacuo for 2 h at room temperature. The residue was dissolved in 30 mL dichloromethane and the solution was stirred vigorously with a solution of 3.48 g (86.9 mmol) of sodium hydroxide in 40 mL water for 30 min. Calcium carbonate (3.48 g) was added to the mixture and it was stirred another 30 min. The organic phase was separated and the aqueous phase was washed with dichloromethane (3×25 mL). The combined organic phases were dried over anhydrous calcium carbonate. The volatile materials were evaporated on a rotary evaporator. The residue was distilled, by 28-30° C./0.25 Torr (lit. bp 69-71° C./13 Torr (see Haug, E. et al. Synthesis, 1983, 35-37)), to yield 4.0 g (32%) of product, 98% pure (GC). IR (neat) 2956, 2929, 286 (C—H), 1629 (N═C) cm−1. 1H NMR 3.17 (t, 2H, JHH 7.2 Hz, —CH2—N═), 2.86 (s, 6H, —N—(CH3)2); 1.87 (s, 3H, —N═C(CH3)—N); 1.5 (m, 2H, —CH—CH2—N═); 1.25-1.4 (m, 6H, CH3—(CH)3—); 0.88 (t, 3H, JHH 7.2 Hz, CH3).

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